Throw off the bowlines and sail towards your dreams

Singapore Escape member Dennis is an aviation engineer who is making plans to transition out of his current job to pursue a different career, one that excites him. His belief is to continuously explore his boundaries and approach life with a “never say die” attitude. Below are his thoughts on how one can plan and make that transition: “Stop Dreaming, Start Planning.”

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbour. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

This quote contains a nice analogy, describing each of us as the Captain of our own ship.

Being the Captain of my ship for 30 years, I have kept my ship anchored to the safety of the harbour, and stayed generally within this comfort zone for a large part of my life. The idea of sailing beyond my comfort zone was a dream until today where I finally decided to leave my job.

There is excitement because my ship can finally stretch her sail and push her boundaries. But there is also fear, because my ship may sink before she even reaches the sea!

The question to ask myself is, Why do I sail? Why risk going to sea when the harbour keeps me safe from the unknowns?

Silencing that Eternal Question

The reason for sailing was the need to silence that eternal question in me. If not now, when?

My dreams and passion were the trade winds that blew my ship out to sea.

Comfort zones and materials needs were the bowlines that anchored me to harbour. As it takes a lot more time and preparation than just waking up one day and deciding to sail, it is important to recognise your bowlines, condition your ship and find the direction of your trade winds before you begin your journey.

Recognising the bowlines

Comfort zone and material needs were the bowlines that anchored me to my job for the last 2 years.

I was performing well in my career and it was paying reasonably well to meet my material needs.

The colleagues in my office were great and there was sufficient time for my family and friends. All these factors fortified my comfort zone, and I allowed life’s demands to push me along from one task to another.

There was minimal need for me to step out of my comfort zone, to think, to plan or to act on what I want in life.

However, the truth is, Comfort zones got me nowhere! The light bulb moment came when I realised all I did was to live my days and weeks in an almost repeated fashion. My life seemed like an old movie played over and over again. I had to break free from the bowlines.

“Things may come to those who wait, but only things left by those who hustle.” — Abraham Lincoln

Conditioning my Ship for Sailing

Recognising my bowlines was only the start.

Having my ship stayed in harbour for so long, she was nowhere near sailable condition. I had to repair my ship, stock up my rations, and gather a crew in order to set sail.

By that, I took up a Master of Science program to retrain my mind, saved up some cash for rainy days, and met new friends who shared with me their journeys and difficulties.

Can I foresee the weather and environment as I sail out to sea? Not really. But have I prepared myself for the journey? You bet I have!

“I will prepare and someday my chance will come” — Abraham Lincoln

Finding the Direction of my Trade Winds

Recognising my bowlines and conditioning my ship have been the easier of task to prepare myself.

Finding the direction of my trade winds that involved defining my dreams and passion was the most difficult and elusive task.

In my own experience, understanding my strengths, exploring my interest, and listening to every single word Steve Jobs made at the Stanford Commencement Speech on YouTube, was probably what led me to define my dreams and passion. “Stay Hungry. Stay Foolish” is what Steve Jobs would say.

Hungry to answer the deepest question of what you want in life, and foolish to explore, dream, and discover yourself. There will be inertia and it will take time. Rome wasn’t built in a day and neither will your dreams be.

“Do what you love and you’ll never work a day” – Confucius

Saying Farewell to the Familiar Harbour…

As I informed my bosses, colleagues and friends of my decision to quit my job as an aviation engineer, I am back to the feeling of excitement and fear.

Just like the first day of school, I do not have the definite answers if I will succeed or fail.

But what I do know is I will be resilient, hardworking and hungry to achieve my goals and dreams.

Love the part about “I hope in these days we have heard the last of conformity and consistency”. And also the final para “Nothing can bring you peace but the triumph of principles”. So true and precious in society today.

Hope everyone who read it can break out of the mould placed over them by society and live their life based on their own principles and beliefs.

About Escape the City

Frustrated by climbing the corporate ladder, we decided to build a community to help people build meaningful careers doing work that matters – to them and to the world. We help talented people find fulfilling work by making big career changes, building businesses, & going on big adventures. We’d love you to come with us on this journey.